(3S,4S)-4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one | 108865-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S)-4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one
• 英文别名: 4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one；(3S,4S)-4-ethyl-3-hydroxy-4-methyldihydro-2(3H)-furanone；(3S,4S)-4-ethyl-3-hydroxy-4-methyloxolan-2-one
• CAS: 108865-89-0
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: UDNSVMRLHHBYOK-VDTYLAMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one 、 2,6-二甲基吡啶 、 光气 、 (3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide 、 三乙胺 在 乙醚 、 盐酸 、 magnesium sulfate 、 silica gel 、 乙酸乙酯 、 hexanes 作用下， 以 乙醚 、 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 21.75h， 以hexanes to afford 170 mg (47%) of (3S,4S)-4-ethyl-4-methyl-2-oxotetrahydro-3-furanyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate的产率得到(3S,4S)-4-ethyl-4-methyl-2-oxotetrahydro-3-furanyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate
  参考文献：
  名称：

  Derivatives of 1-(oxoaminoacetyl) pentylcarbamate as cathepsin K inhibitors for the treatment of bone loss

  摘要：

  本文描述了公式（I）的杂环取代酮酰胺衍生物，其中替代物A、D、A和R如权利要求中所定义，这些衍生物对于作为卡他普星K抑制剂是有用的。所述发明还包括制备这种杂环取代酮酰胺衍生物的方法，以及使用它们制造治疗与骨吸收和形成不平衡相关的疾病，包括骨质疏松症，最终可能导致骨折的药物的方法。

  公开号：

  US07402606B2
• 作为产物：
  描述：

  (2,1')E,5S,6R-4,5-dimethyl-2-(1-methylpropylidene)-6-phenylmorpholin-3-one 在 三乙基硅烷 、 硫酸 、 氨 、 水 、 sodium 、 三溴化硼 、 四氯化钛 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 36.09h， 生成 (3S,4S)-4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Enantioselective synthesis of pantolactone analogues from an ephedrine-derived morpholine-dione

  摘要：

  An efficient enantioselective synthesis of beta,beta-dialkyl alpha-hydroxy gamma-butyrolactones, analogues of pantolactone, has been developed employing a stereoselective Prins reaction of chiral alkylidene morpholinones, as the key step. Enantioselective synthesis of a naturally occurring pantolactone homologue and a spiro analogue of pantolactone was achieved with this protocol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00408-3

文献信息

• Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands
  作者：Frederic Bourgeois、Jonathan A. Medlock、Werner Bonrath、Christof Sparr

  DOI：10.1021/acs.orglett.9b04033

  日期：2020.1.3

  A catalyst repurposing strategy based on a sequential aldol addition and transfer hydrogenation giving access to enantiomerically enriched α-hydroxy-γ-butyrolactones is described. The combination of a stereoselective, organocatalytic step, followed by an efficient catalytic aldehyde reduction induces an ensuing lactonization to provide enantioenriched butyrolactones from readily available starting

  描述了基于顺序的醛醇加成和转移氢化的催化剂再利用策略，该策略允许获得对映异构体富集的α-羟基-γ-丁内酯。立体选择性的有机催化步骤的组合，然后是有效的催化醛还原，引起随后的内酯​​化，以从容易获得的起始原料中提供对映体富集的丁内酯。通过利用脯氨酸酰胺既充当有机催化剂又充当转移加氢配体的能力，催化剂的再利用允许开发一种操作简单，经济且有效的顺序催化方法。
• Derivatives of 1-(oxoaminoacetyl) pentylcarbamate as cathepsin k inhibitors for the treatment of bone loss
  申请人：Barrett Gene David

  公开号：US20050245596A1

  公开（公告）日：2005-11-03

  Heterocycle substituted ketoamide derivatives of Formula (I), wherein the substitutes A, D, A and R are defined as in claim in, which are useful as cathepsin K inhibitors are described herein. The described invention also includes methods of making such heterocycle substituted ketoamide derivatives as well as method of using the same in the manufacture of medicaments for the treatment of disorders, including osteoporosis, associated with an imbalance between bone resorption and formation which can ultimately lead to fracture.

  本文描述了公式(I)的杂环取代酮酰胺衍生物，其中替代基A、D、A和R如权利要求中所定义，这些衍生物可用作卡特普西林K抑制剂。所述发明还包括制备这种杂环取代酮酰胺衍生物的方法，以及使用它们制造治疗与骨吸收和形成失衡有关的疾病（例如骨质疏松症），最终可能导致骨折的药物的方法。
• Enantioselective synthesis of β,β-dialkyl α-hydroxy γ-butyrolactones
  作者：Sunil V Pansare、Annyt Bhattacharyya

  DOI：10.1016/s0040-4039(01)01979-7

  日期：2001.12

  An ephedrine-derived morpholine dione is employed in the synthesis of chiral alkylidene morpholinones that are efficiently converted to beta -substituted alpha-gamma -dihydroxy butyramides, precursors of the corresponding butyrolactones. Enantioselective synthesis of a spiro analog of pantolactone as well as a naturally occurring pantolactone homolog is achieved with this protocol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and absolute configuration of (+)-hyperolactone B
  作者：Toshihiko Ueki、Daisuke Ichinari、Kazuo Yoshihara、Yoshiki Morimoto、Takamasa Kinoshita

  DOI：10.1016/s0040-4039(97)10713-4

  日期：1998.2

  The synthesis of (+)-hyperolactone B2, isolated from Hypericum chinense L., was accomplished from (S)-malic acid. This synthesis unambiguously established the absolute stereochemistry of hyperolactone B. (C) 1998 Elsevier Science Ltd. All rights reserved.
• KINOSHITA, TAKAMASA;HIRANO, MADOKA;MIYAKE, HIROYUKI, J. HETEROCYCL. CHEM., 28,(1991) N, C. 619-624
  作者：KINOSHITA, TAKAMASA、HIRANO, MADOKA、MIYAKE, HIROYUKI

  DOI：——

  日期：——